


Derek Hale the Fail Wingman

by whenshewrites



Series: A Collection of One-Shots and Tumblr Prompts [42]
Category: Teen Wolf (TV)
Genre: Accidental Wingmanning Situations, Alpha Derek Hale, Angst, Derek Hale Loves Stiles Stilinski, Derek Hale is Bad at Feelings, Derek Hale is a Mess, Derek is Derek, Fluff, Humor, Idiots in Love, M/M, Misunderstandings, Mutual Pining, One Shot, Originally Posted on Tumblr, Stiles Just Wanted Coffee, Stiles Stilinski Loves Derek Hale, Stiles Stilinski is a Little Shit, Stiles Stilinski is a Mess, That's an accurate tag, Tumblr Prompt
Language: English
Status: Completed
Published: 2020-07-10
Updated: 2020-07-10
Packaged: 2021-03-04 19:00:21
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,071
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25171258
Author URL: https://archiveofourown.org/users/whenshewrites/pseuds/whenshewrites
Summary: Stiles was pretty sure kissing Derek counted as progress. But then Derek tried to set him up with someone new three days later.
Relationships: Derek Hale/Stiles Stilinski
Series: A Collection of One-Shots and Tumblr Prompts [42]
Series URL: https://archiveofourown.org/series/1956889
Comments: 26
Kudos: 569





	Derek Hale the Fail Wingman

Stiles kissed Derek first.

He’d always thought that one day, after the man got his head out of his ass and realized Stiles was downright irresistible, Derek would be the one to initiate things. But then at the beginning of senior year, after a summer of Stiles spending every waking moment at the loft, Derek still hadn’t done anything.

So Stiles kissed him first. He thought he was allowed to do that.

And the thing was, Derek responded.

Stiles liked to believe that one day, he’d break down all of the Sourwolf’s walls. He knew he’d gotten even further this summer than he ever had before, but Derek was a fortress. Just when Stiles thought he’d broken down the man’s last level of grumpy-growly defense, he was faced with a whole other line of barriers.

One day, Stiles thought. One day, he’d get the man to fully trust him. But for now, he thought things were good enough.

Except, he forgot Derek was a hard-headed asshole.

“This,” Derek said, coffee in hand and a brown-haired woman standing at his side, “is Amy.”

Stiles blinked intelligently at her for a moment. Her cheeks were pink and she looked nervous, the barista’s apron wrapped around her waist. Stiles supposed it wasn’t ‘Amy’ who surprised him, but the fact that Derek knew anybody outside of his little loft hidey-hole.

Also, that the man was introducing them. Maybe he was proud of making a new friend?

Derek waited with a raised eyebrow and Stiles blinked out of his thoughts, pushing a half-hearted grin onto his face as he nodded, not quite sure where this was going. Derek confused him sometimes. “Okay.”

Some of Amy’s smile faded. Derek shot him a warning look. “Stiles, this is that friend I was telling you about.”

‘Derek’ and ‘friend’ still took Stiles off guard. He supposed if he thought about it, Derek had mentioned meeting someone at the cafe a few weeks ago. He’d said something about how she was ‘nice’ and ‘funny’. Stiles was pretty sure he’d been complaining about his single woes from Sophomore year, then. He hadn’t really been listening to Derek or himself, to be honest.

Sometimes, Stiles just felt the need to talk.

“Oh,” Stiles said. Then a sudden panicked realization hit him like a truck. _ “Oh.” _

Derek’s forced smile looked more murderous than usual. But before Stiles could make up an excuse to run, Amy was stepping forward, Derek was stepping back, and Stiles was left alone with no coffee and apparently a… a... wait, was Derek  _ wingmanning him? _

Stiles’s stomach did something entirely new and he was pretty sure he wasn’t okay with it.

Amy started to say something but Stiles’s mind had gone blank. Three days ago, he and Derek had been making out on the couch and now the man was trying to set him up? Or maybe… maybe… no, the kissing had not been a fever dream. Stiles had gone right home afterward and proceeded to have a panic attack followed by the literal eating of a giant tub of ice cream in celebration.

His dad had been giving him strange looks ever since.

“Stiles?”

Stiles snapped out of his thoughts, looking at Amy with round eyes. She held out a slip of paper with her number on it and he stared for a moment, before plastering another grin on his face and taking the paper from her hands.

“So you’ll pick me up at seven?”

“Seven?”

Amy’s smile flickered. “For dinner at that new Italian place I was just telling you about.”

“Oh,” Stiles said. “Um, oh, yeah. Italian! Love Italian. Yeah, I’ll be there. At seven. Because this is a date?”

Amy was looking a lot less impressed now than she was five minutes ago. Stiles thought that was usually how things went when he talked to girls, wingmanned or not. But she still nodded and then turned away, moving back behind the cafe counter.

Stiles just stood there for another few moments, staring at the slip of paper in his hands as his brain tried to catch up.

Derek had just wingmanned him. Derek Hale has just wingmanned him. Then left. And now Stiles was going on a date. Tonight.

“Oh my god,” Stiles said, shoving the number into his pocket.

That stubborn-headed Alpha bastard.

-

Stiles showed up at the loft a lot later that night with a suit jacket hanging off one shoulder, a tie half undone, and exhaustion under his eyes that he couldn’t even begin to explain.

Derek sat on the couch and tensed up the moment he spotted him in the doorway. Stiles held his gaze for a long moment before trudging over and dropping down at his side with a sigh. If possible, Derek tensed even more.

“Did you have a… good date?”

“Dude,” Stiles said, glancing over. “I think my wallet is crying.”

Derek’s brows furrowed. Stiles leaned heavily against his side, just wanting to burrow up and maybe sleep for the next day or two. 

It wasn’t like anything had gone wrong, exactly. In fact, Stiles would say he’d been the proper gentleman. He’d shown up on time, he’d paid for dinner and dessert. They’d walked around town after and when Amy told him things ‘just weren’t like she’d expected’ Stiles nearly full on agreed. But he was a gentleman. So he’d just nodded, driven her home, and decided he was never letting Derek wingman him again.

Which really shouldn’t be a decision he had to make.

“I just want curly fries and sleep,” Stiles said. “But that restaurant was so expensive, I don’t think I can even afford curly fries right now.”

“So… it didn’t go well?”

Stiles glared at him. “I blame you for this.”

“What.”

“Dude!” Stiles said, drawing back a few inches. “What?  _ What?  _ When you said ‘let’s go get coffee’ this morning, I expected to be walking out with a nice hot mocha, not a date!”

Derek gave him a blank look. “I told you days ago this was happening.”

“Uh, when?”

“When I told you Amy was looking for someone and you said ‘oh yeah, I know that feeling’.”

“Because I do! I have! Not now, but—”

“Then I told you I could try and set something up and you gave me a funny look and said ‘yeah, Sourwolf, you do that’ and proceeded to walk out of the loft.”

Stiles blinked at him. For some reason, those words did sound familiar, but he wouldn’t go around saying something like that unless… “Dude, I was joking! Are you serious right now? I’m like, ninety percent sure we had just finished making out before that conversation!”

Derek stared. Then his face turned bright red, he frowned even harder, and proceeded not to say another word. Stiles shoved himself off the couch, throwing his hands up.

“Oh my god, Derek! Are you serious?”

“What.”

“Stop ‘what-ing’ me! Do you really think I go around kissing people and then letting them set me up with someone else? That’s a douchebag move. That’s a Jackson move!”

The man looked at him with a blank expression. Stiles scoffed and turned away, waving a hand over his shoulder.

“You know what, fine dude, whatever. I’m going to go beg spare change from my own father because I’m in desperate need of curly fries but I can’t even  _ afford  _ any right now. Please, feel free to make up a list of everyone else you think I should attempt dating. Clearly I need it.”

Derek didn’t answer. Stiles gave him one more look over his shoulder but the man just crossed his arms, arching one brow. Stomach twisting, Stiles stalked out of the loft and made sure to slam the door behind him.

He was tired earlier. Now he was downright pissed.

When he made it to his jeep, he didn’t drive for a long moment. Instead, he glared at nothing and tried to keep himself from stalking right back up to the loft. What the hell did Derek think they were? What the hell did he think Stiles had wanted in the first place?

He tried to replay the last few weeks over again in his head. The first time Stiles had kissed him; all nerves and a sudden rush of adrenaline. Then small kisses on the couch, or in the kitchen, or when Stiles came by the loft after school.

And Stiles… Stiles hadn’t known what exactly to call it. 

They didn’t mention anything to the pack but Stiles thought that might just take time. And Derek didn’t really acknowledge anything was happening until Stiles was kissing him, but he thought maybe that was just another one of the man’s walls.

Sighing, Stiles dropped his forehead against the steering wheel. Was he the idiot here?

No, he couldn’t be. It was the hard-headed, grumpy growly, big bad Alpha werewolf who was most likely up angsting in the loft and—

A knock on his window startled Stiles out of his thoughts. He squawked, head snapping upward, and his elbow banged on the steering wheel, the alarm almost instantly going off. Derek jumped back and Stiles swore, quickly turning it off.

For a moment, they just stared at each other. Then, groaning, Stiles opened his door and pulled himself back into the night, crossing his arms against the faint chill.

“What, Derek?”

“You weren’t checking me off a list.”

Stiles stared at him for a long moment before finding words. Derek’s face turned bright red and the man dropped his gaze. “What?”

“You weren’t checking me off a list or experimenting with… another gender, or—”

“Dude, what the hell?”

Derek looked up, a ‘caught in headlights’ look in his eyes. Stiles swallowed hard, searching his face. 

“That’s what you thought I was doing?”

“You’re a teenager, Stiles, it’s the expected and conventional behavior of—”

“Conventional,” Stiles said, cutting him off. 

Derek nodded.

“Oh my god,” Stiles said, rubbing a hand over his face. To be honest, he really should have seen this coming. One of Derek’s biggest walls was ‘I’m not deserving of actual love’ but Stiles had been hoping he’d broken that one down already. Apparently not. “Derek, nothing about us is conventional.”

Derek just looked confused. Stiles sighed and stepped forward, tilting his chin upward.

“You’re a big bad grumpy Alpha werewolf. I’m the token human with a baseball bat who Isaac compares much too often to Little Red Riding Hood. We fight monsters every other week and attempt to live normal lives in between. Also, I’m eighteen now. I’m like, a couple years away from getting grey hairs.”

Derek rolled his eyes at that. Stiles grinned, reaching up to brush the pad of his thumb across the man’s lower lip.

“Also you’re like, really hot. I’ve been wanting you to kiss me since Sophomore year and if we’re being honest, I kissed you first with the hopes that we could keep doing that. For a long time. Like, a really long time. Like, maybe until we actually do have grey hairs and—”

Derek moved forward and cut him off, slightly chapped lips pressing against his own. Stiles startled for only a second before melting into the man’s touch, his hand moving to cup the back of Derek’s neck.

“You,” Derek said around his lips, breaths warm against his skin. “Stiles, I want you too.”

“Good, you big idiot, because I’ve been pining for two years now—”

Derek seemed to notice how effectively he could shut Stiles up by just kissing him. Because the man only growled at the back of his throat and pushed Stiles against the jeep, one hand catching a handful of his hair and tilting his head back a few inches before kissing him harder.

Stiles wasn’t really complaining. 

And yeah, he thought Derek was kind of a big idiot. But to be fair, he could be too. And maybe it took two years, one chaotically pining summer, and an accidental wingmanning situation, but Stiles was pretty sure he’d broken down another wall tonight,

There were probably more. 

Like, a lot more. Like enough to give him grey hairs even as a teenager more. But Stiles might be a little okay with that. One day, he thought, he’d get the man to fully trust him. One day, he’d break down all of Derek’s walls. But for now, things were good enough. 

Derek was always enough.

**Author's Note:**

> Based on the prompt "Nothing about us is conventional" and I had a ton of fun with this one! Derek being a confused softie is my favorite thing ever. Of course, I'd love to hear what you guys thought!
> 
> Come hang with me on Tumblr?
> 
> [the dumpster](https://when-she-writes-stuff.tumblr.com/)


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